Can ChatGPT help me write an investor email?
Short answer
Yes, an AI tool can help you draft and tighten an investor email. But it cannot make a weak email compelling. The email still needs to be concise, unique and clear, with a call to action. I use AI mostly to grade a draft before it goes out, the way I would bounce it off a business partner.
Yes, it can help. I would use it to draft, then to critique, then to cut. The tool is not the hard part. The hard part is writing an email that an investor will actually answer.
Why most investor emails get ignored
At Family Office Club we run a database business, and we hear the same thing often. Someone emails 10 investors from an event or from the database, gets few replies, and assumes the investors did not like the email. Usually the email was the problem.
Many people who pitch a deal write an essay. No one has time to read it. Pitch decks have the same issue. A 44 page or 77 page deck is usually too long. Even your own partners will not read every word.
"You still have to write an email that gets people value, or is unique, or is exciting and compelling and high conviction. And part of that is just being concise."
What I check before an investor email goes out
I built an investor email analyzer based on feedback from 1,500 investors who have spoken on stage at our events. It also reflects what I have learned over 18 years of running our investor club and sending emails to our CRM of well over 100,000 people.
This clip shows the investor email analyzer grading a sample email on subject line, call to action, uniqueness and signature.
Summary and key takeaways from this video
You paste in an email and it grades it. It judges the subject line. It suggests a call to action. It looks at investor appeal and how unique the message is. It also checks whether you have an email signature. I programmed it to flag any email longer than two to three sentences as not concise enough.
Think of it as bouncing the draft off a business partner before you hit send.
What good investor emails look like in practice
Personal and short beats polished and long. At one of our live rating sessions, a guest named Jason shared that his firm sends about 100,000 emails to portfolio companies. A partner uses the subject line "Are you alive?" and gets candid replies quickly.
Another attendee emailed a friend with a subject line that asked if he would be at an event on Monday. It read as a short, personal note. Long emails with graphics take more than a minute or two to read, so they get snoozed or archived.
In this clip, investors react live to one-liners and short emails and talk about what makes them work.
Summary and key takeaways from this video
I also tell people to include tangible numbers that can be verified. Investors cannot tell if you started yesterday or have done 457 deals unless you say so. Keep the numbers inside a short, clear statement.
A few cautions
Be careful what you paste into any AI tool. Big companies that host your email or documents could in theory see your data. Our tools have the box unchecked so conversations do not feed the model. Check the settings on whatever tool you use. And many sponsors talk to a securities attorney about any offer language before it goes out to investors.
From the Family Office Club stage
The shortest version of this is a sentence and a half. When I want an asset owner's attention, I write one line saying what I would like to do, whether that is invest, join the board, become a strategic partner, or buy the business. Then I stop. Think about who is reading. A busy investor with hundreds of other emails will not get through an essay, and a Yahoo address with a clipart logo makes the note look like it came from the 1990s before they read a word.
"If you email someone with a Yahoo email address and your clipart logo, it's like it's from the 1990s. And if you write them an essay-long email, Candace doesn't have time to read that. She has 600 other emails to get through."
"You write a sentence and a half email that gets the attention of that asset owner, saying you'd like to invest, become a board member, or a strategic partner, or buy their business."
Facts from this talk
- Our investor email analyzer is based on feedback from 1,500 investors who spoke on stage at Family Office Club events.
- The analyzer is programmed to flag any investor email longer than two to three sentences as not concise enough.
- One firm sends about 100,000 emails to portfolio companies, and one partner uses the subject line "Are you alive?" to get quick, candid replies.
Sources
From Richard C. Wilson's Centimillionaire Strategies YouTube channel: Webinar: Demonstration of 10 Artificial Intelligence Tools for Capital Raisers & Investors, Webinar: Demonstration of 10 Artificial Intelligence Tools for Capital Raisers & Investors, Live Investor Ratings: Hear investor first impressions on your brand name, and/or 10-second pitch. Quotes come from the video captions, lightly edited for readability. Figures are the speakers' own estimates and experience.
General education only. Not legal, tax or investment advice.
Talk to a securities attorney to explore options around offer language, investor communication rules and offering terms disclosure. Do not use AI to write your own legal agreements.
What to do next
- Draft your email in two to three sentences with one clear ask.
- Write a subject line that feels personal, not like a mass blast.
- Add one or two verifiable numbers such as years in business or deals done.
- Run the draft through an AI tool and ask it to grade the subject line and call to action.
- Many sponsors talk to a securities attorney about language on returns or offering terms before sending.
More questions on this
How long should an investor email be?
Short. I programmed our email analyzer to flag anything longer than two to three sentences as not concise enough. Most investors have no time to read an essay.
Should I put my numbers in the email?
Yes, if they can be verified. Investors cannot tell if you have done two deals or 457 unless you say so. Keep it inside a short statement.
Is my data safe in an AI tool?
It depends on the tool and its settings. Big platforms could in theory use your data. In our tools we unchecked the box that shares conversations with the model. Check the settings on any tool you use.
Related questions
- Can AI automate investor follow-up sequences?Yes, AI can automate much of the routine work in investor follow-up, like scheduled emails, reminders and tracking who replied.
- How do I use AI to build a fundraising financial model?Use AI as a fast assistant for drafting the structure, formulas and scenarios of your model, then check every number yourself.
- Will AI replace placement agents and capital raisers?Probably not fully.
- How do I use AI to write investor update newsletters?Give the AI your real source material, such as deal notes, closings and milestones, and ask it for a first draft in your own voice.
Work through it with the family office fit check. See all ai for capital raising resources.